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Volumn 120, Issue 18, 1998, Pages 4439-4449

Reaction of organic sulfides with singlet oxygen. A revised mechanism

Author keywords

[No Author keywords available]

Indexed keywords

OXYGEN; SULFIDE; SULFOXIDE;

EID: 0032513702     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja973782d     Document Type: Article
Times cited : (157)

References (62)
  • 5
    • 0002393586 scopus 로고
    • Baumstark, A. L., Ed.; JAI Press: Greenwich, CT
    • Jensen, F. In Advances in Oxygenated Processes; Baumstark, A. L., Ed.; JAI Press: Greenwich, CT, 1995; Vol. 4, pp 1-48.
    • (1995) Advances in Oxygenated Processes , vol.4 , pp. 1-48
    • Jensen, F.1
  • 6
    • 0001806360 scopus 로고
    • Baumstark, A. L., Ed.; JAI Press: Greenwich, CT
    • Clennan, E. L. In Advances in Oxygenated Processes; Baumstark, A. L., Ed.; JAI Press: Greenwich, CT, 1995; Vol. 4, pp 49-80.
    • (1995) Advances in Oxygenated Processes , vol.4 , pp. 49-80
    • Clennan, E.L.1
  • 9
    • 2642653552 scopus 로고    scopus 로고
    • note
    • Previous calculations at the MP2/6-31G(d) level did not provide a good match for the observed frequencies (ref 9). We have improved the theoretical level to MP2/6-311+G(2df), with only minor changes in calculated frequencies and isotopic shifts. Frequencies for the S-hydroperoxysulfonium ylide 4 have also been calculated, but these do not agree with experimental values either.
  • 19
    • 33746614482 scopus 로고
    • An additional set of tight d-functions was added to sulfur
    • Dunning, T. H., Jr. J. Chem. Phys. 1989, 90, 1007-1023. An additional set of tight d-functions was added to sulfur.
    • (1989) J. Chem. Phys. , vol.90 , pp. 1007-1023
    • Dunning Jr., T.H.1
  • 33
    • 2642597389 scopus 로고    scopus 로고
    • note
    • The MP2/6-31G(d) natural occupation numbers for the HOMO-LUMO orbitals are 1.94 and 0.05, respectively.
  • 44
    • 2642632063 scopus 로고    scopus 로고
    • Ph.D. Thesis, University of Wyoming
    • Greer, A. Ph.D. Thesis, University of Wyoming, 1996.
    • (1996)
    • Greer, A.1
  • 57
    • 2642598358 scopus 로고    scopus 로고
    • note
    • The [10,10]-CASSCF/6-31G(d) natural occupation numbers for the HOMO-LUMO orbitals are 1.22 and 0.78, respectively, at the MP2/6-31G(d) geometry. The corresponding CCSD(T) values are 1.25 and 0.69.
  • 62
    • 2642696096 scopus 로고    scopus 로고
    • note
    • A kinetic isotope effect for sulfone, but not sulfoxide, formation may still be possible with a S-hydroperoxysulfonium ylide as a common precursor if the sulfone formation step has a substantially larger isotope effect than the intermolecular trapping step for formation of the sulfoxide. The calculated value for the sulfone step of 2.6 would mean that the intermolecular trapping should occur essentially without an isotope effect.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.